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Spirofluorene derivative type organic compound and application thereof to organic light-emitting diodes

A technology of electroluminescent devices and organic compounds, which is applied in the field of spirofluorene derivative organic compounds and their application in organic electroluminescent devices, and can solve the problems of different performances, etc.

Active Publication Date: 2019-05-31
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.

Method used

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  • Spirofluorene derivative type organic compound and application thereof to organic light-emitting diodes
  • Spirofluorene derivative type organic compound and application thereof to organic light-emitting diodes
  • Spirofluorene derivative type organic compound and application thereof to organic light-emitting diodes

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Embodiment 1: the synthesis of intermediate II and intermediate VI

[0066] a. Synthesis of Intermediate II

[0067]

[0068] (1) Under the protection of nitrogen, weigh raw material A and dissolve it in tetrahydrofuran, cool to -78°C, then add 1.6mol / L tetrahydrofuran solution of n-butyllithium to the reaction system, react at -78°C for 3h, then add Triisopropyl borate, react for 2 hours, then raise the reaction system to 0°C, add 2mol / L hydrochloric acid solution, stir for 3 hours, the reaction is complete, add ether for extraction, add anhydrous magnesium sulfate to the extract to dry, rotary evaporate, use ethanol solvent recrystallization to obtain intermediate B; the molar ratio of raw material A to n-butyllithium is 1:1-1.5; the molar ratio of intermediate S4 to triisopropyl borate is 1:1-1.5.

[0069] (2) Under nitrogen protection, weigh intermediate B, Fe(NO 3 ) 3 .9H 2 O, dissolved in toluene; heated to 90-110°C, reacted for 10-24 hours, took a sample p...

Embodiment 2

[0102] Embodiment 2: the synthesis of compound 5:

[0103]

[0104] (1) In a 250ml three-neck flask, under the protection of nitrogen, add 0.05mol raw material I-1, 0.075mol intermediate II-1, dissolve with a mixed solvent (90ml toluene, 45ml ethanol), and then add 0.15mol Na 2 CO 3 aqueous solution (2M), stirred under nitrogen for 1 hour, then added 0.0005mol Pd(PPh 3 ) 4 , heating to reflux for 15 hours, sampling point plate, the reaction is complete. Naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain intermediate III-1 with a purity of 99.0% and a yield of 78.1%. Elemental analysis structure (molecular formula C 40 h 27 NO 3 ): theoretical value C, 84.34; H, 4.78; N, 2.46; O, 8.43; test value: C, 84.32; H, 4.77; N, 2.47; ESI-MS(m / z)(M + ): The theoretical value is 569.20, and the measured value is 569.44.

[0105] (2) In a 100ml three-necked flask, under the protection of nitrogen, add 0.03mol interme...

Embodiment 3

[0107] Embodiment 3: the synthesis of compound 12:

[0108]

[0109] (1) In a 250ml three-neck flask, under the protection of nitrogen, add 0.05mol of raw material I-1, 0.075mol of intermediate II-2, dissolve with a mixed solvent (90ml of toluene, 45ml of ethanol), and then add 0.15mol of Na 2 CO 3 aqueous solution (2M), stirred under nitrogen for 1 hour, then added 0.0005mol Pd(PPh 3 ) 4 , heating to reflux for 15 hours, sampling point plate, the reaction is complete. Naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain intermediate III-2 with a purity of 99.6% and a yield of 77.4%. Elemental analysis structure (molecular formula C 40h 27 NO 2 S): Theoretical value C, 82.03; H, 4.65; N, 2.39; O, 5.46; S, 5.47; Test value: C, 82.05; ESI-MS(m / z)(M + ): The theoretical value is 585.18, and the measured value is 585.38.

[0110] (2) In a 100ml three-neck flask, under the protection of nitrogen, add 0.03mol in...

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Abstract

The invention relates to a spirofluorene derivative type organic compound and application thereof to organic light-emitting diodes (OLEDs). The spirofluorene derivative type organic compound has the advantages that spirofluorene is in loop connection with an indole ring fusion structure through carbon-carbon double bonds, the loop connection through the carbon-carbon double bonds increases material chemical stability and avoids branch chain group active position exposure, and the whole molecule is a large rigid structure and has high triplet-state energy level (T1); the indole ring fusion structure is large in steric hindrance, less prone to rotation and stable in three-dimensional space structure, and accordingly the compound is high in glass transition temperature and molecular thermal stability; in addition, the HOMO and LUMO distribution positions of the compound are separated from each other, so that the compound has appropriate HOMO and LUMO energy level; after the compound is applied to the OLEDs, the light-emitting efficiency of the OLEDs can be effectively increased, and the service life of the OLEDs can be effectively prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a spirofluorene derivative organic compound and its application in organic electroluminescent devices. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. The OLED light-emitting device is like a sandwich structure, including electrode material film layers and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. OLED light-emitting devices are current devices. When a voltage is applied to the electrodes at both ends, and the positive an...

Claims

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Application Information

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IPC IPC(8): C07D491/113C07D497/10C07D491/107C07D498/10C07D495/10C07D513/10C07D471/10C07D209/96C07D487/10C07D405/12C07D409/12C07D403/12C07D405/04C07D409/04C09K11/06H01L51/50H01L51/54
CPCC07D209/88C07D405/04C09K11/06C07D409/12C09K2211/1088C09K2211/1092C09K2211/1029H10K85/636H10K85/633H10K85/6574H10K85/6576H10K85/6572H10K50/18H10K50/11
Inventor 唐丹丹张兆超李崇张小庆
Owner JIANGSU SUNERA TECH CO LTD
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